EP2503878B1 - Polyurée dendritique pour la solubilisation de substances actives difficilement solubles - Google Patents

Polyurée dendritique pour la solubilisation de substances actives difficilement solubles Download PDF

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Publication number
EP2503878B1
EP2503878B1 EP10781507.8A EP10781507A EP2503878B1 EP 2503878 B1 EP2503878 B1 EP 2503878B1 EP 10781507 A EP10781507 A EP 10781507A EP 2503878 B1 EP2503878 B1 EP 2503878B1
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EP
European Patent Office
Prior art keywords
polymer
polyethylene glycol
polyurea
amphiphile
linear
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
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EP10781507.8A
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German (de)
English (en)
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EP2503878A1 (fr
Inventor
Holger TÜRK
Monika Haberecht
Hiroe Yamada
Bernd Bruchmann
Daniel SCHÖNFELDER
Michael Ishaque
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BASF SE
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BASF SE
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3234—Polyamines cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds

Definitions

  • cosmetic active ingredients are cosmetic oils, fragrances and flavorings, vitamins or UV absorbers.
  • Cosmetic oils include peanut oil, jojoba oil, coconut oil, almond oil, olive oil, palm oil, castor oil, soybean oil or wheat germ oil or essential oils such as mountain pine oil, lavender oil, rosemary oil, pine needle oil, pine needle oil, eucalyptus oil, peppermint oil, sage oil, bergamot oil, turpentine oil, lemon balm oil, juniper oil, Lemon oil, aniseed oil, cardamom oil, camphor oil etc. or mixtures thereof.
  • Amphiphiles usually contain at least one polar (hydrophilic) and at least one apolar (hydrophobic) part. Typical amphiphiles are fatty acids, surfactants and phospholipids. The composition may contain one or more different amphiphiles.
  • AB x monomers are suitable for the synthesis of these hyperbranched polymers.
  • These have two different functional groups A and B, which can react with each other to form a linkage.
  • the functional group A is contained only once per molecule and the functional group B twice or more times.
  • By the reaction of said AB x monomers with one another uncrosslinked polymers are formed essentially having regularly arranged branching points.
  • the polymers have almost exclusively B groups at the chain ends. More details are for example in Journal of Molecular Science, Rev. Macromol. Chem. Phys., C37 (3), 555-579 (1997 ) to find.
  • These oligo-or polyisocyanates usually have an average NCO functionality of 2.1 to 4.9, preferably 2.9 to 4.4, in particular 3.4 to 3.9.
  • the average molecular weight is usually from 300 to 3000 g / mol, preferably from 400 to 1500 g / mol, in particular from 500 to 800 g / mol.
  • the reaction ratio at 1: 1 the result is a molecule of the type XY.
  • the preparation of the condensation product (A) from a capped diisocyanate and a trivalent amine at a conversion ratio of 1: 1 results in a molecule of the type XY 2 .
  • Focal group here is a capped isocyanate group.
  • the production of the condensation product (A) from a capped diisocyanate and a tetravalent amine also with the conversion ratio 1: 1 results in a molecule of the type XY 3 .
  • Focal group here is a capped isocyanate.
  • amine as a focal group
  • a mono-, di- or polyurethane, a mono-, di- or polyisocyanate, an aldehyde, ketone or an amine-reactive acid derivative may be added to the product (P).
  • di-C 1 -C 20 alkyl esters of fumaric acid and maleic acid such as dimethyl fumarate, dimethyl maleate, dibutyl and dibutyl maleate, glycidyl monoethylenically unsaturated monocarboxylic acids having preferably 3 to 6 carbon atoms, such as glycidyl acrylate and glycidyl methacrylate.
  • Preferred further monomers are the esters with C 1 -C 10 -alkanols of acrylic acid and methacrylic acid.
  • the other block contains polyesters (eg based on a dicarboxylic acid and a diol), polyamide (eg based on a dicarboxylic acid and a diamine), polycarbonate, polyurethane or polyurea.
  • Preferred block polymers are polyethylene glycol block polycaprolactone and polyethylene glycol monomethyl ether blockpolycaprolactone and polyproylene glycol block polyethylene glycol.
  • Suitable initiators are organic hydroperoxides such as tert-butyl hydroperoxide, tetrahydrofuran hydroperoxide, cumene hydroperoxide or 2,2'-azobis (2-methyl-N- (2-hydroxyethyl) propionamide).
  • Suitable regulators are amino alcohols, aminophenols and in particular thioalkanols such as 3-hydroxypropanethiol, 3-mercapto-1,2-propanediol, 2-hydroxyethyl-3-mercaptopropionic acid ester and especially 2-hydroxyethanethiol (mercaptoethanol).
  • Preferred solvents are butyl acetate, tetrahydrofuran, xylene and acetone.
  • the reaction is usually carried out at elevated temperatures, wherein the temperature also depends on the boiling point of the selected solvent.
  • the reaction of the polyisocyanate with the first component can be carried out at 20 to 80 ° C, but if desired also up to 100 ° C, provided that the first component has a hydroxyl group as a linker-reactive group.
  • Stage 2 146.4 g of the reaction product A.2a and 36.4 g of isophoronediamine were initially charged with gassing with dry nitrogen. After addition of 0.1 g of potassium hydroxide (dissolved in 2 ml of n-butanol) as a catalyst, the reaction mixture was heated with stirring to 150 ° C and stirred for 12 h at this temperature before the reaction was stopped by cooling to RT.
  • potassium hydroxide dissolved in 2 ml of n-butanol

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Polyethers (AREA)

Claims (17)

  1. Composition contenant un amphiphile et un agent actif, qui est soluble dans l'eau à 20 °C à hauteur d'au plus 10 g/l, caractérisée en ce que l'amphiphile contient une polyurée dendritique, qui est reliée avec au moins un polymère linéaire ou en forme de peigne, et la liaison a lieu par le biais d'un lieur bifonctionnel si les unités de répétition du polymère linéaire sont constituées d'oxyde d'alkylène polymérisé.
  2. Composition selon la revendication 1, dans laquelle le polymère linéaire est
    a) un homopolymère ou un copolymère statistique contenant un monomère éthyléniquement insaturé polaire,
    b) un polymère séquencé contenant une séquence de polyéthylène glycol ou à base d'un monomère éthyléniquement insaturé polaire ou
    c) un polycondensat contenant un polyéthylène glycol ou
    d) un polyéthylène glycol,
    le polyéthylène glycol d) étant relié par un lieur bifonctionnel avec la polyurée.
  3. Composition selon la revendication 1 ou 2, dans laquelle le polymère linéaire est
    a) un homopolymère ou un copolymère statistique contenant un monomère éthyléniquement insaturé polaire,
    b) un polymère séquencé contenant une séquence de polyéthylène glycol ou à base d'un monomère éthyléniquement insaturé polaire, ou
    c) un polycondensat contenant un polyéthylène glycol.
  4. Composition selon la revendication 2 ou 3, dans laquelle le monomère éthyléniquement insaturé polaire est la vinylpyrrolidone, l'acide (méth)acrylique, un monomère contenant de l'acide sulfonique, un monomère à fonction amino ou un ester de l'acide (méth)acrylique d'un dérivé de polyéthylène glycol.
  5. Composition selon l'une quelconque des revendications 1 à 4, caractérisée en ce que le polymère en forme de peigne contient un mono(méth)acrylate de polyéthylène glycol ou un alcoxylate d'alcool allylique sous forme polymérisée.
  6. Composition selon l'une quelconque des revendications 1 à 5, dans laquelle l'agent actif est un pesticide.
  7. Composition selon l'une quelconque des revendications 1 à 6, dans laquelle la polyurée dendritique est de préférence une polyurée hyperramifiée.
  8. Composition selon la revendication 7, dans laquelle la polyurée hyperramifiée peut être obtenue par un procédé comprenant la mise en réaction d'un diou polyisocyanate bloqué au moins bifonctionnel avec au moins une amine primaire et/ou secondaire au moins bifonctionnelle avec élimination de l'agent de blocage.
  9. Composition selon l'une quelconque des revendications 1 à 7, caractérisée en ce que l'agent de blocage est un monoalcool.
  10. Amphiphile contenant une polyurée dendritique, caractérisé en ce que la polyurée dendritique est reliée avec au moins un polymère linéaire ou en forme de peigne et la liaison a lieu par le biais d'un lieur bifonctionnel si les unités de répétition du polymère linéaire sont constituées d'oxyde d'alkylène polymérisé.
  11. Amphiphile selon la revendication 10, dans lequel le polymère linéaire est
    a) un homopolymère ou un copolymère statistique contenant un monomère éthyléniquement insaturé polaire,
    b) un polymère séquencé contenant une séquence de polyéthylène glycol ou à base d'un monomère éthyléniquement insaturé polaire ou
    c) un polycondensat contenant un polyéthylène glycol ou
    d) un polyéthylène glycol,
    le polyéthylène glycol d) étant relié par un lieur bifonctionnel avec la polyurée.
  12. Amphiphile selon la revendication 10 ou 11, dans lequel le polymère en forme de peigne contient un mono(méth)acrylate de polyéthylène glycol sous forme polymérisée.
  13. Amphiphile selon l'une quelconque des revendications 10 à 12, dans lequel la polyurée dendritique est de préférence une polyurée hyperramifiée.
  14. Amphiphile selon la revendication 13, dans lequel la polyurée hyperramifiée peut être obtenue par un procédé comprenant la mise en réaction d'un di- ou polyisocyanate bloqué au moins bifonctionnel avec au moins une amine primaire et/ou secondaire au moins bifonctionnelle avec élimination de l'agent de blocage.
  15. Amphiphile selon la revendication 13 ou 14, dans lequel un oligo- ou polyisocyanate d'une masse molaire moyenne de 300 à 3 000 g/mol est utilisé en tant que di- ou polyisocyanate.
  16. Procédé de fabrication de l'amphiphile selon l'une quelconque des revendications 10 à 15 par
    a) mise en réaction de la polyurée dendritique avec le polymère linéaire ou en forme de peigne ou
    b) mise en réaction de la polyurée dendritique avec un monomère qui peut former par polymérisation par ouverture de cycle une partie du polymère linéaire ou en forme de peigne.
  17. Procédé de fabrication de la composition selon l'une quelconque des revendications 1 à 9, par mise en contact de l'amphiphile et de l'agent actif.
EP10781507.8A 2009-11-27 2010-11-23 Polyurée dendritique pour la solubilisation de substances actives difficilement solubles Not-in-force EP2503878B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10781507.8A EP2503878B1 (fr) 2009-11-27 2010-11-23 Polyurée dendritique pour la solubilisation de substances actives difficilement solubles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09177370 2009-11-27
PCT/EP2010/067978 WO2011064185A1 (fr) 2009-11-27 2010-11-23 Polyurée dendritique pour la solubilisation de substances actives difficilement solubles
EP10781507.8A EP2503878B1 (fr) 2009-11-27 2010-11-23 Polyurée dendritique pour la solubilisation de substances actives difficilement solubles

Publications (2)

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EP2503878A1 EP2503878A1 (fr) 2012-10-03
EP2503878B1 true EP2503878B1 (fr) 2015-01-28

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EP10781507.8A Not-in-force EP2503878B1 (fr) 2009-11-27 2010-11-23 Polyurée dendritique pour la solubilisation de substances actives difficilement solubles

Country Status (10)

Country Link
US (1) US9725554B2 (fr)
EP (1) EP2503878B1 (fr)
JP (1) JP2013512294A (fr)
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CA2781637A1 (fr) 2011-06-03
AU2010323241A1 (en) 2012-06-14
JP2013512294A (ja) 2013-04-11
EP2503878A1 (fr) 2012-10-03
WO2011064185A1 (fr) 2011-06-03
CN102612318B (zh) 2015-01-07
CN102612318A (zh) 2012-07-25
BR112012011915B1 (pt) 2019-09-10
US9725554B2 (en) 2017-08-08
US20120238641A1 (en) 2012-09-20
KR20120114234A (ko) 2012-10-16
BR112012011915A2 (pt) 2015-10-13

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